#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:30:04 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301811 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/00/32/4003204.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4003204
loop_
_publ_author_name
'Kawashima, Kazuaki'
'Osaka, Itaru'
'Takimiya, Kazuo'
_publ_section_title
;
 Effect of Chalcogen Atom on the Properties of
 Naphthobischalcogenadiazole-Based π-Conjugated Polymers
;
_journal_issue                   19
_journal_name_full               'Chemistry of Materials'
_journal_page_first              6558
_journal_paper_doi               10.1021/acs.chemmater.5b03124
_journal_volume                  27
_journal_year                    2015
_chemical_formula_moiety         'C20 H12 N4 S2 Se2'
_chemical_formula_sum            'C20 H12 N4 S2 Se2'
_chemical_formula_weight         530.38
_chemical_name_common            NSz2T
_chemical_name_systematic
; 
NSz2T
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.6026(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.8022(2)
_cell_length_b                   4.60300(10)
_cell_length_c                   22.6036(4)
_cell_measurement_reflns_used    1657
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      68.16
_cell_measurement_theta_min      3.91
_cell_volume                     915.77(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      101(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_sigmaI/netI    0.0494
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8915
_diffrn_reflns_theta_full        68.16
_diffrn_reflns_theta_max         68.16
_diffrn_reflns_theta_min         3.91
_exptl_absorpt_coefficient_mu    7.303
_exptl_absorpt_correction_T_max  0.9306
_exptl_absorpt_correction_T_min  0.0676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.923
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.745
_refine_diff_density_min         -1.001
_refine_diff_density_rms         0.163
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.896
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1657
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.896
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0765P)²+2.2907P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.1057
_reflns_number_gt                1540
_reflns_number_total             1657
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cm5b03124_si_004.cif
_cod_data_source_block           NSz2T
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_atom_site_symetry_multiplicity' was replaced with
'_atom_site_symmetry_multiplicity' as specified in the replacement
file
'/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/lists/replacement-tags.lst'.

Automatic conversion script
Id: cif_correct_tags 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4003204
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.0728(3) 0.5431(6) -0.00686(12) 0.0107(6) Uani 1 1 d .
C2 C 0.1962(3) 0.4036(6) 0.02546(12) 0.0106(6) Uani 1 1 d .
C3 C 0.1634(4) 0.1909(7) 0.07196(13) 0.0120(6) Uani 1 1 d .
C4 C 0.0068(3) 0.1078(6) 0.08392(11) 0.0103(6) Uani 1 1 d .
C5 C -0.1038(4) 0.2427(5) 0.05107(14) 0.0116(7) Uani 1 1 d .
H1 H -0.2066 0.1916 0.0579 0.014 Uiso 1 1 calc R
C6 C -0.0303(3) -0.1100(6) 0.12845(12) 0.0112(6) Uani 1 1 d .
C7 C 0.0636(4) -0.2677(6) 0.16517(14) 0.0131(7) Uani 1 1 d .
H2 H 0.1712 -0.2532 0.1646 0.016 Uiso 1 1 calc R
C8 C -0.0167(3) -0.4569(6) 0.20464(12) 0.0145(6) Uani 1 1 d .
C9 C -0.1693(3) -0.4424(6) 0.19570(12) 0.0134(6) Uani 1 1 d .
H3 H -0.2406 -0.5539 0.2173 0.016 Uiso 1 1 calc R
C10 C 0.0623(4) -0.6424(7) 0.25011(13) 0.0166(6) Uani 1 1 d .
H4 H 0.0869 -0.5246 0.2850 0.025 Uiso 1 1 calc R
H5 H 0.1561 -0.7209 0.2335 0.025 Uiso 1 1 calc R
H6 H -0.0045 -0.8028 0.2615 0.025 Uiso 1 1 calc R
N1 N 0.2854(3) 0.0856(6) 0.09975(11) 0.0155(5) Uani 1 1 d .
N2 N 0.3401(3) 0.4620(5) 0.01569(10) 0.0143(5) Uani 1 1 d .
S1 S -0.21925(9) -0.19988(16) 0.14098(3) 0.0135(2) Uani 1 1 d .
Se1 Se 0.44915(4) 0.24873(6) 0.067170(14) 0.01597(19) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 C1 C5 122.6(3) 3_565 3_565
C1 C1 C2 116.8(3) 3_565 .
C5 C1 C2 120.6(3) 3_565 .
N2 C2 C1 122.8(3) . .
N2 C2 C3 117.0(3) . .
C1 C2 C3 120.2(3) . .
N1 C3 C4 125.3(3) . .
N1 C3 C2 114.7(3) . .
C4 C3 C2 120.1(3) . .
C5 C4 C6 121.5(3) . .
C5 C4 C3 116.7(3) . .
C6 C4 C3 121.7(3) . .
C4 C5 C1 123.5(3) . 3_565
C4 C5 H1 118.2 . .
C1 C5 H1 118.2 3_565 .
C7 C6 C4 130.0(3) . .
C7 C6 S1 110.2(2) . .
C4 C6 S1 119.8(2) . .
C6 C7 C8 113.5(3) . .
C6 C7 H2 123.2 . .
C8 C7 H2 123.2 . .
C9 C8 C7 111.7(3) . .
C9 C8 C10 125.5(3) . .
C7 C8 C10 122.8(3) . .
C8 C9 S1 112.6(2) . .
C8 C9 H3 123.7 . .
S1 C9 H3 123.7 . .
C8 C10 H4 109.5 . .
C8 C10 H5 109.5 . .
H4 C10 H5 109.5 . .
C8 C10 H6 109.5 . .
H4 C10 H6 109.5 . .
H5 C10 H6 109.5 . .
C3 N1 Se1 107.6(2) . .
C2 N2 Se1 106.79(19) . .
C9 S1 C6 91.93(14) . .
N1 Se1 N2 93.95(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C1 1.381(6) 3_565
C1 C5 1.432(4) 3_565
C1 C2 1.452(4) .
C2 N2 1.316(4) .
C2 C3 1.468(4) .
C3 N1 1.330(4) .
C3 C4 1.458(4) .
C4 C5 1.367(5) .
C4 C6 1.460(4) .
C5 C1 1.432(4) 3_565
C5 H1 0.9500 .
C6 C7 1.372(4) .
C6 S1 1.740(3) .
C7 C8 1.438(4) .
C7 H2 0.9500 .
C8 C9 1.357(4) .
C8 C10 1.502(4) .
C9 S1 1.720(3) .
C9 H3 0.9500 .
C10 H4 0.9800 .
C10 H5 0.9800 .
C10 H6 0.9800 .
N1 Se1 1.790(2) .
N2 Se1 1.793(2) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C1 C1 C2 N2 178.6(3) 3_565 .
C5 C1 C2 N2 -0.9(4) 3_565 .
C1 C1 C2 C3 -2.5(5) 3_565 .
C5 C1 C2 C3 178.1(3) 3_565 .
N2 C2 C3 N1 1.3(4) . .
C1 C2 C3 N1 -177.8(3) . .
N2 C2 C3 C4 -177.9(3) . .
C1 C2 C3 C4 3.0(4) . .
N1 C3 C4 C5 179.3(3) . .
C2 C3 C4 C5 -1.6(4) . .
N1 C3 C4 C6 -1.1(5) . .
C2 C3 C4 C6 178.0(2) . .
C6 C4 C5 C1 -179.8(3) . 3_565
C3 C4 C5 C1 -0.3(4) . 3_565
C5 C4 C6 C7 179.8(3) . .
C3 C4 C6 C7 0.2(5) . .
C5 C4 C6 S1 -0.6(4) . .
C3 C4 C6 S1 179.8(2) . .
C4 C6 C7 C8 178.2(3) . .
S1 C6 C7 C8 -1.4(3) . .
C6 C7 C8 C9 1.5(4) . .
C6 C7 C8 C10 -177.9(3) . .
C7 C8 C9 S1 -0.8(3) . .
C10 C8 C9 S1 178.5(2) . .
C4 C3 N1 Se1 178.2(2) . .
C2 C3 N1 Se1 -0.9(3) . .
C1 C2 N2 Se1 178.1(2) . .
C3 C2 N2 Se1 -0.9(3) . .
C8 C9 S1 C6 0.1(2) . .
C7 C6 S1 C9 0.8(2) . .
C4 C6 S1 C9 -178.9(2) . .
C3 N1 Se1 N2 0.3(2) . .
C2 N2 Se1 N1 0.3(2) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 122388286
